Posted on 04 June 2011 | 2 Comments

Ever wanted to low-key flirt with your best friend?

Dear MISSter Simms,

I’m 23 years old and have been best friends with this guy I’ve known since the 5th grade. He’s seen me at my best; he’s seen me at my worst. Everything that goes down in my life he pretty much knows about and vice versa Our relationship has been pretty much platonic all the years, but recently I’ve started to look at him in a new light. The problem is I have no idea if he’s thought about us as being anything more than friends, and I definitely don’t want to ruin something that’s been good all these years. If I flirt with him maybe I can get a better sense of how he feels, but how can I do it so it’s more subtle than obvious?

Wannabe Flirt

Dear Wannabe,

Ah yes, the age old dilemma: how to flirt with a friend without ruining what’s made things work in the first place. Even ancient cave dwellers had a pickle of a time trying to solve the problem. Luckily for you, you’ve got semi-professional relationship advice columnist on your side, one who also happens to be a master at subtle flirting techniques. Kinda comes in handy when you’re trying to get discounts at Target (don’t ask). Here are some acts that I feel could be useful on your quest of ascertaining how your BFF actually feels about you:

Compliment Him: Don’t overdo it now or you’ll tip him off. Just throw out a compliment here and there, maybe once or twice a week. And keep them innocuous. Bad idea: “My, your ass looks particular supple today!” Good idea: “That shirt looks good on you.”

Get Physical: By getting physical I 100% do not mean tackle him like a football player and rip his pants off. As tempting as that sounds, it would be better to do smaller gestures, like rubbing on him when you’re cold, rubbing him up when he’s cold, or smoothing his hair back when it’s out of place.

Be Thoughtful: This kind of walks the line between flirting and being a good friend, but getting or doing things for your friend that they’ll like is actually an ultra subtle form of flirting. If you friend loves playing basketball, for instance, offer to play a game with him one on one or ask him to teach you how to play if you haven’t before.

Tell Him How Awesome He Is: This goes along with complimenting his looks, but don’t forget to compliment the other things you like about him. You know, things that are the reasons why you’re BFF in the first place. Maybe it’s his laugh. Maybe it’s his Baryshnikov like dance moves. Whatever it is, tell him how much you love it. It’s flirty but also true, right?

Dress Up: Whenever you go out with him don’t be afraid to thrown on your finest…whatevers. And I don’t mean like you’re going to church on Easter Sunday. I’m talking about stuff you could conceivably wear on a night out on the town. More often than not it’ll grab his attention and he’ll start flirting with you, giving you the perfect opening to use your own, subtle, ninja like flirting techniques.

Need relationship advice? Send your questions to ronsimmsjr at gmail dot com and you might be featured on the next installment of Ask MISSter Simms.